Studying while I'm Shopping for a Gen2?

Hello, all.
I've finally come toward the end of my Ridgeline's useful life to me (300k), and am looking to up-size. I've had my Toyota experience with my wife's 2008 4Runner Limited V8, and we just purchased her a 2016 Tacoma Offroad Double Cab. Now I'm driving the 4Runner until I can settle on just the right Tundra. I'm thinking that I want a Gen 2 due to the balance of age and cost (under $20k), although I wouldn't be opposed to going to Gen 1 or Gen 3 if there is a compelling argument in either of those directions.
Being in Michigan, I definitely want 4x4, and would like to get leather, but that's not a deal breaker. As far as which engine, I haven't figured out yet what the advantages/disadvantages are, or if the 5.7 is the only way to go. I will tow a travel trailer, and my current trailer is sub 6000 lbs, but might upgrade down the road.
Thanks, and I'll just be wandering around and reading, hopefully before I post any dumb questions.
Don

 

Welcome from NY.
Good luck with your search.

 

Welcome!

 

Welcome!...You can find a Gen 3 in the mid 20's you will have to do extensive search though and perhaps travel a bit to find it.
Mostly the interior updates is what made me go for the Gen 3.

 

And welcome from

 

Welcome from TX!

 

Welcome from NC! 5.7 is the way to go!

 

Welcome from da bay

 

Welcome from CO

 

Welcome to the party!!!

 

Welcome, do not get the 4.6 if you plan on towing especially if possible upgrade. You'll never say I wish I got the smaller engine...

 

5.7, the 4.6 doesn't gain you anything besides an engine that is harder to find parts and has no aftermarket support. There's a considerable price jump between 2 and 3. If you don't plan on doing a lot of towing I would seriously consider a 1st gen. The 2nd gen has a ton of annoying quirks I found that I'm only finally getting fixed. The transmission shifting is horrible, it can't hold a gear to save it's life and you'll be in cruise control and go through 3 gears because you glanced at a hill, the seat belt chimes forever if you have something in the passenger seat, the throttle is jerky and inconsistent, etc. My dad's 2005 felt a lot more refined than my 2008, to the point I considered selling it for awhile, and I got it purely for the larger engine for towing cars around. All food for thought. I bought mine at 180k for $15k with no issues. At 220k now and added a supercharger and Kings and tuned it and went in with techstream and changed stuff and finally it's fun to drive imo. Point being, imo, I'd be open to any generation.